


Dear Theodosia, You're so Hot

by Honey_Masquerade



Category: Hamilton - Miranda
Genre: ??? - Freeform, Alternate Universe - High School, F/M, First Time, High School, I'm Going to Hell, I'm Sorry, Loss of Virginity, Plot What Plot/Porn Without Plot, Riding, School Uniforms, Semi-Public Sex, Sex, Underage Sex, Vaginal Sex, What Was I Thinking?, Why Did I Write This?, awkward freshman philip, don't be like them, i couldn't find the correct philip tag, i guess, they are dumb high schoolers, they moved too fast
Language: English
Status: Completed
Published: 2016-11-18
Updated: 2016-11-18
Packaged: 2018-08-31 17:44:39
Rating: Mature
Warnings: Underage
Chapters: 1
Words: 2,835
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8587885
Author URL: https://archiveofourown.org/users/Honey_Masquerade/pseuds/Honey_Masquerade
Summary: In which Theodosia and Philip do it for the first time in the prop room.





	

**Author's Note:**

> This is the first oneshot I've written and I don't even know why I did it. But here goes nothing. I should be working but instead I'm writing smut.

High school was supposed to be an amazing four years filled with parties, sport championships, and girls. It was supposed to be his time to shine as the quarterback of the varsity football team, leading the team to victory. It was supposed to be his time when party invitations would fall into his lap. It was supposed to be his time to be the most popular kid in school.. But none of that was what freshman Philip Hamilton was experiencing. He was not the quarterback on the varsity team, he didn’t even play sports, he was on the debate team. He was never invited to parties and was nowhere close to being the most popular kid in school. To be perfectly honest, many of his fellow students couldn’t stand the kid. He was nothing more than an awkward freshman. Though he complained, he did have someone who always brightened his day.

Theodosia Burr.

Theodosia Burr was a sophomore and member of the drama club with beautiful, thick, curly brown hair and stunning dark skin. Philip thought she looked like a queen. Her eyes sparkled and her smile made him melt. They had several classes together, and he found himself falling for the girl early on in the school year. His father had taught him to go after what he wanted with bravery and determination, so one day after school, as the sixteen year old was walking to her car, Philip confessed to her. The boy, still only fourteen at the beginning of the school year, presented her with a small bouquet of tulips. He remembered how fast his heart had been racing, the heat in his cheeks, how sweaty his palms were. It was a terrifying few seconds as Theodosia stared at him in shock. Then she broke out into a smile, a blush coming to her own dark cheeks, and a beautiful giggle rang out like bells. She met Philip’s eyes and took the flowers, confessing her own feelings for the boy, telling her how much she admired his passion. They had been dating secretly for four months, not wanting to tell their parents. Alexander Hamilton and Aaron Burr were rivals at a local newspaper and the children were afraid they would be forced apart if their fathers discovered their relationship. They wrote notes to each other. Theodosia’s were lovely and thought out, usually written in pink pen. Philip’s were not so well thought out. He was not gifted with the same writing skill as his father had been and most of his letters were a mess. But Theodosia cherished each one of them, and giggled at the ridiculous things he wrote to her. Her favorite had to be “Dear Theodosia, you’re so hot.” She found Philip’s awkwardness to be charming. Philip walked Theodosia to class every day and would walk her to her car after school. Theodosia would stand outside the debate room to listen to him recite his arguments and bring him water and food from home. They would occasionally meet outside of school at the movies or the bowling alley, but they had to be careful.

Their first kiss was shared in the school theater when Theodosia had asked him to come watch her practice a monologue. She had pulled him behind the curtains and pressed their lips together, a deep blush on her cheeks. Their kiss had been clumsy, but they were smiling with joy when it ended. Philip could remember what Theodosia had said: “We’ll just have to practice and get better.” And they did get better. They would meetup and makeout in the theater, in the janitor’s closet, in empty classrooms, in the gym, wherever they could. Being hormonal teenagers, they began to practice more than kissing on the lips. The kisses traveled to their necks, then slowly to Theodosia’s breasts. She would unbutton her school blouse and let Philip fondle her chest and unclip her bra so he could suck on her dark nipples. Theodosia had started giving him handjobs in the beginning of their second month of dating, blowjobs in the end. By month three Theodosia was letting him finger her. And now, in their fourth month, they were ready for more.

It was a Thursday, both the debate team and drama club had practices after school. As Theodosia passed Philip by his locker, she slipped a note into his hand and gave a smile. Philip slung his backpack over his shoulder and looked at the note as he walked to practice.

“Philip, meet me in the prop room after your practice. We’ll be alone ;). I’ll be counting the minutes until you arrive.” The note read. Philip turned red and shoved the note into his pocket. Oh my god, it was going to happen. It was really going to happen! He was going to lose his virginity! Philip hurried to the debate room, as if thinking that the quicker he got there the quicker it would be over. Of course, when you are waiting for something to come, it always feels like it takes forever to arrive. He was distracted all during debate, imagining what Theodosia was doing as she waited for him. Her practice ended fifteen minutes before his, so she had time to herself. He imagined what he would do to her. He would… He would… What would he do? A sudden, horrific realization came to him. He had no idea what he was supposed to do during sex! He had fallen asleep during sexual education and had never asked his father about any of this. It was a little embarrassing, but Philip usually relied on Theodosia to tell him what he was supposed to do. God, she was going to think he was an idiot… He closed his eyes and thought about every bit of porn he had seen, which honestly wasn’t much. He knew that he had to be inside of her and move his hips… Was that it? No, it couldn’t be. There had to be more to it, right? He thought about how the women in the porn clips would moan and began imagining Theodosia moaning his name.

“Philip… Philip…”

“Aw yeah…” it was practically a moan as it slipped from the boy’s mouth.

“Philip… Philip Hamilton.”

“Say my name…”

“I am, now you say your cut.” The words made Philip jump. His debate coach as staring at him, an eyebrow raised. The other team members snickered and Philip felt his cheeks heat up. He had really spaced out, how embarrassing.

“S-Sorry…” Philip stood and started reciting his argument. He was incredibly grateful for when the practice came to an end. Philip grabbed his bag and raced out of the classroom as his teammates mocked him with fake moans. He looked down and hurried to the auditorium. The stage was set for the winter play of Romeo and Juliet. Theodosia was playing Juliet, of course, and Philip couldn’t wait to see her in it. He walked up onto the stage and into the wings and then backstage. He stood in front of the prop room door, nervous butterflies in his stomach. This was it, this was going to happen… Theodosia Burr was waiting on the other side, waiting to take him into her, to snatch his virginity and let him snatch her’s. He stood there, breathing deeply, trying to calm his nerves, when the door opened and Theodosia grabbed his backpack strap and pulled him inside the prop room, shutting the door behind her. She stood on her toes and gave him a deep kiss.

“Your practices take too long… I was getting really impatient.” She smiled at him and Philip noticed how dilated her pupils were and the flush on her cheeks. “I kept thinking about you…” He dropped his backpack and she took his hand and brought it to her inner thigh. He blushed, feeling how wet she was. Her smile was devilish.

“Theodosia…” His voice came out as a low rumble, his fingers traveled to her womanhood. “I’m sorry you had to wait…” He rubbed gently, a good way to start this out, he thought. He knew how to please her with his fingers at least. Theodosia leaned on him and moaned and Philip’s fingers rubbed at her clit and dipped between her folds.

“Oh… Philip… Philip, I don’t have much time… My dad is expecting me to meet with him at the grocery store in half half an hour. If we want to do this, we have to start now so I can run to the showers in the gym before I leave.”

“Mm… That’s a good point. My mom will be coming to pick me up around then too.” Philip said. He blushed and looked at his girlfriend. “How do we do this?”

“I’ll lead you through it.” Theodosia said, smiling sweetly. She had done her research to make sure their first time would be safe and comfortable. The girl handed him a condom. “First you need to get that on, that’s our top priority. I’ll get myself ready for you.” Philip took the condom and removed his pants and boxers. He blushed, still feeling shy about Theodosia seeing him like this, even though she had given him many blowjobs before. He struggled with slipping the condom on, his shaking hands fumbling with the slippery rubber. When he had finally gotten it on, he looked over at Theodosia. She had set up a few blankets to try to make the concrete floor more comfortable for them. Her uniform was folded neatly beside her along with her panties and bra. Her kneesocks and school shoes were still on. She beckoned her boyfriend over to her and he come obediently. Philip had gotten hard just from looking at her, her beautiful naked form waiting for him. He crawled on top of her and kissed her passionately. Theodosia spread her legs as they kissed and pulled him closer and closer until she felt the tip of his penis brush against her cunt. Philip pulled away from the kiss and looked down at where they were meeting.

“What do I do?” He asked softly.

“Push in, Philip. Push through my hymen and then just move your hips back and forth… They may be some blood when the hymen breaks..” Theodosia told him. Philip nodded. He gripped his member and pushed into her very slowly. Her mouth formed a perfect “o” and she squeezed her eyes shut as he pushed his way inside of her. He groaned and gripped her hips when he felt the resistance of her hymen. “Push through…” Theodosia groaned. Philip gripped her hips tighter and, with a hard push, broke through. Theodosia moaned in pain as it broke.

“Dosia, are you okay?” Philip asked her with concern. She opened her eyes and smiled at him.

“I’m fine, just give me a moment.” She said reassuringly. Philip waited for her, but once he became accustomed to how she felt around him, he found it hard to stay still. He felt like her warmth was drawing him in, trying to get him to push the rest of the way inside. He was so grateful when Theodosia spoke again. “Okay, I’m ready. You can start moving.” Philip nodded. In and out, in and out, in and out. It wouldn’t be hard, he could do this. He moved his hips back, pulling out until only the tip of his penis was left inside of her, then he pushed back inside completely. They both let out a moan of pleasure and Philip felt encouraged to continue. He pulled out and thrust back in, getting a little faster with each motion. He set a quick pace and fucked the girl, his girl, his girlfriend, his queen, his Juliet. Yes, she was his Juliet, and he, her Romeo. They were in love, though their parents were rivals. Her slender fingers twisted into the blankets beneath them. He leaned down and kissed her as the sound of skin slapping against skin filled the small prop room. Theodosia moaned into the kiss and gripped Philip’s curly brown locks tightly as she wrapped her legs around his waist. She pulled away from the kiss and moaned his name. “Philip… Philip… Philip!” The moans fell from her kiss swollen lips. The sound of her saying her name drove him crazy. He sped up his movements and felt heat rising.

“Oh fuck, Theodosia!” Philip cried out as he buried himself deep inside of her and came, his seed filling his condom. He panted, tired and not really wanting to pull out of the warmth that was Theodosia. She stroked his cheek.

“Philip… That was amazing… But I didn’t orgasm yet.” She told him. “Can you help me?” Philip grinned and pulled out of her. She groaned at the loss, feeling empty, but her groans of unhappiness quickly changed to pleasure when she felt her Romeo’s tongue against her cunt. Philip had only eaten her out once before, in the janitor’s closet before school earlier in the month, and besides sex now, it was her favorite thing that he did to her. He pressed his tongue flat against her and licked all around, tasting her arousal and his presence in her. He flicked his tongue over her clit and relished the sound of her moan his name. He licked and suckled at it, practically speaking French between her legs. She grabbed his hair again and arched her back, screaming out his name as she came, her essence wetting his face. She collapsed against the blankets and panted. Philip sat back and used a blanket to wipe his face and between her legs, making sure they were both at least a little clean. He removed the condom and was about to toss it in the trash when Theodosia snatched it from him. She opened it up and held it over her mouth, letting the cum drip in. She kept eye contact with Philip as she drank his seed from the condom. She licked her lips and smiled when she saw him become half hard again. Theodosia giggled and looked at the time on her phone.

“We have time for one more round.” She pulled out a second condom and opened it up. Theodosia pushed her boyfriend back onto the blanket and leaned over his cock. She stroked him and leaned down to suck at the tip, making sure he was fully hard. She slipped the condom on him with ease and sat up on her knees, moving so she was straddling him, his dick right below her. She gripped it and looked into his eyes as she lowered herself onto him. Philip cursed in French as her warmth surrounded him once more. He felt like they melted together perfectly. Theodosia lowered herself completely, taking all of him into her. “I love this… I love feeling so full… Love knowing it’s you filling me…” She placed her hands on his stomach for leverage and rose her hips up before slamming back down and eliciting a strangled moan from Philip. Theodosia did it again, and then again. She bounced on his dick, riding him like her life depended on it. Philip was an average size, but she was in love with the way he stretched her out, the pressure it gave and the pleasure that flowed through her body. She leaned back and continued to let her hips rise and fall. Philip propped himself up on his elbows and watched. He experimentally thrust up and the moan that came from Theodosia’s lips was delicious. He gripped her hips and proceeded to thrust up into her cunt. Theodosia threw her head back and moaned, the sound of her saying his name sounding like a chant, a prayer. He thrust up into her, his balls slapping against her skin.This time, because she was still sensitive from before, Theodosia came around Philip’s cock. The tightness as she squeezed him caused Philip to bury himself inside of her again and spill his seed into the condom.

Theodosia panted and slowly got off of him, feeling a soreness in her hips. She cleaned herself off with the blanket and helped work the condom off of Philip. This time she simply tied it and shoved it and the first condom into an empty soda can so it wouldn’t be discovered in the trash. She cleaned Philip and they helped each other dress. She shoved the soiled blanket into her backpack so she could wash it and then return it to the prop room. She folded the other blankets and put them away. Theodosia took a hairbrush out of her bag and brushed her hair and then Philip’s. “There, you look very handsome.” She gave him a soft, loving kiss and put the hairbrush away. “That was amazing, Philip… I love you.”

“I love you too, Theodosia.” Philip replied. They shared another loving kiss.

“Will you walk me to the gym?” She asked him.

“Anything for my Juliet.”

**Author's Note:**

> And there you go. I hope you enjoyed it. I do plan on writing more smut oneshots so if you have any ideas of stuff you would like to see, let me know! Thank you for reading!


End file.
